I'm surprised they have any vacancy at all - in the other markets where I have these kinds of properties, we have 100% occupancy and a unit stays vacant for at MOST 2 months. 

@Edgar Butler Jr it is very dependent on what your comfort level is when dealing with equity.

But what about when a landlord files for eviction, and then the tenant pays the past due rent, either before the court date or at the court date, allowing them to stay and continue their tenancy.

Discounting their rent may encourage them to stay longer, but it may also encourage them to take advantage or you or treat your $1,500 rental like a $1,300 rental.

That's worth having a high-quality tenant and it should be worth it to them to avoid moving, paying more, or potentially winding up with a nasty Landlord.If there's even a chance they would cry over an increase, be prepared to show them comparables, the value of staying with you, and how much you are losing by keeping them at the lower rate.

Stay focused. 

I have stayed pretty up to date on material costs, and do not think I’m over estimating myself out of deals.

They can help with gentrifying areas and where to stay out of.

I have stayed pretty up to date on material costs, and do not think I’m over estimating myself out of deals.

Ideally looking to be oceanfront or close to it with purchase price less than 500k, with the goal of having a "house hack" seasonal vacation rental for seniors or company extended stay sort of thing which would pay mortgage, taxes and HOA.